Vacation rentals in Tappan

Large 3BR Sleepy Hollow Apt, Walk to Legend Sites

Welcome to Rock Hollow Loft, a spacious 2,200 sq ft apt steps from the legend that gave Sleepy Hollow its name. Walk 7-8 min to Philipsburg Manor & Old Dutch Church, Cemetary, setting of Irving’s “Legend of Sleepy Hollow.” RiverWalk 15 min on foot, near downtown shops & restaurants. Walking distance to train NYC 40 min Vaulted ceilings, cozy wood burning stove fill the open living space. Kitchen & dining seat 8-10. Sleeps 8: king, full & two twin beds across 3 bedrooms, plus a living room couch.

Location · Hospitality · Indoor spaces

Piermont Getaway Mt. Village Home. 30 min to NYC

Nestled at the base of Tallman Mountain lies the quaint village of Piermont where a population of 2,500 sleep, live & thrive enjoying life on the simpler side. Sip coffee on the porch overlooking the Sparkill creek. Stroll down Main Street to visit an array shops/restaurants. Fishing on the pier, dancing fireflies at night and wildlife throughout. A quick hike along the firetrail to the state park will overlook the backyard mountain, a view of the Hudson & catching a glimpse of NYC or a picnic.

Location · Value · View

Spacious 3b/3b Mediterranean in White Plains

Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!

Family · Value · Heating

Waterfront Luxury in Town

Renovated, waterfront home minutes walking to all of downtown Piermont! Wonderful indoor & outdoor living. Tons of restaurants, bars & cafes walking & quick 15 minute drive to NYC train - the best of both! Huge master with King bed & 2 guest queen bedrooms. Loft space with 2 double beds, office and bonus hangout space. Open floor plan main living room, dining room & kitchen, over looking the Hudson River. Massive private outdoor space - 2 decks, patio & yard running right up to the water!

Family · Value · River

Aspen In Airmont

Welcome to "Aspen in Airmont", a unique lakeside cabin experience in Airmont, NY. Offering 9 beds across 4 rooms, including a lavish Master Suite with Tempurpedic mattresses, a Jacuzzi and separate shower. Our home is Highlighted by a 16-seat dining area, cozy indoor fireplace, and outdoor fire pit. Fits Small/Large Groups. Enjoy the year-round hot tub and in-ground trampoline. The perfect getaway with Friends/Family for vacation or Shabbos. (Located within an Eiruv, close to a local Shul)

Location · Family · Access

Hudson River Suite - Dobbs Ferry

Bright, modern 1BR in the heart of Dobbs Ferry on a quiet street—just 6 mins walk from the train to NYC (30 mins to Grand Central). Open-concept layout with river views, high-speed WiFi & separate bedroom with a work desk. Walk to the best cafes, restaurants, bars, riverfronts, shops and trails. Easy street parking right out front. Ideal for remote workers, couples, families and creatives seeking a stylish, peaceful stay with easy access to the city. Sleeps up to 4. No outdoor access.

Location · Family · Quiet

Sweet & Cozy Home | Free parking

Public transportation just minutes away—bus steps from the home and train very close. Sweet & Cozy Home only 30 minutes from Manhattan. Welcome to your home away from home in Yonkers, NY. This two-floor apartment is perfect for families or groups, offering three comfortable bedrooms, a fully equipped kitchen, a cozy living room with Smart TV, and a private porch for morning coffee or evening relaxation. Easy commute to Manhattan, Bronx Zoo, Yankee Stadium, and other NYC attractions.

Family · Value · Nearby

Hudson River Views | Private Balcony+ 2 Gyms

Wake up to stunning Hudson River views from this thoughtfully designed 1 bedroom apartment with a private balcony. Just a 10 minute walk to Metro North with Grand Central only 25 to 30 minutes away. Enjoy two fitness centers, a resort style pool, rooftop lounges, fast WiFi, and a fully equipped kitchen. Perfect for business trips, weekend getaways, or exploring NYC without staying in Manhattan. Staying for the FIFA Club World Cup Final? MetLife Stadium is only 30 minutes away.

Location · View · Accuracy

Modern 5BR 3 Full Bath, Fits 10 guests near NYC

Welcome to your home away from home! This newly furnished retreat features a brand-new kitchen, beautifully renovated bathrooms, modern furnishings, and bright, inviting spaces throughout. Enjoy the huge outdoor patio and fully equipped outdoor kitchen, perfect for relaxing or entertaining. Conveniently located near New York City and just 20 minutes from MetLife Stadium, it’s the perfect getaway for families, friends, and travelers seeking comfort and style.

Family · Location · Sleep quality

Peaceful 5 Bedroom 3 Bathroom House, 30 min to NYC

Beautiful newly renovated 5 bedroom, 3 bathroom home in quaint town 30 minutes to NYC. Perfect for a family getaway, friends trip or remote work! Enjoy hotel quality bedding, central AC, fully stocked kitchen, Smart TVs, dedicated work space, and enjoy some grilling outdoors on the patio. 30 min commute to NYC, Tuckahoe Metronorth station within walking distance, and beautiful playgrounds and parks nearby!

Family · Location · Outdoor spaces

Luxury 3BR • Sleeps 10 • Walk to Metro • Parking

Enjoy the perfect location! My place is just a few minutes’ walk to the Metro North train, making it easy to be in New York City in about 30 minutes. You’ll be close to everything — supermarkets, restaurants, coffee shops, and parks — all within a convenient distance. Ideal for guests who want comfort, accessibility, and quick travel into Manhattan.

Family · Location · Kitchen

Idyllic & Chic in Piermont, 20 min from GW Bridge

Idyllic and charming home located in the Village of Piermont, a river town along the Hudson Valley, just 20 minutes from the George Washington bridge. Our home is right in town, set back from the main st yet steps away from the Bunbury coffee shop, restaurants, stores and a 5 min walk to the Hudson River and Tallman Park.

Family · Location · Access